Benzoic acid, 4-[(3-methyl-2-butenyl)oxy]-, ethyl ester → Ethyl 3-(1,2-dimethyl-allyl)-4-hydroxy-benzoate

HRID 1625306Notes

Reaction equation

HRID 1625306 reaction equation
CC(C)=CC[O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1>C1(OC)C=CC=CC=1>[CH3:7][CH:8]([C:16]1[CH:15]=[C:9]([CH:8]=[CH:7][C:6]=1[OH:5])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:9]([CH3:15])=[CH2:10]

Participants

3

Reactant 1

HCID 13203109Benzoic acid, 4-[(3-methyl-2-butenyl)oxy]-, ethyl ester

Product 1

HCID 59382270Ethyl 3-(1,2-dimethyl-allyl)-4-hydroxy-benzoateYield 53.7%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Ethyl 4-(3-methyl-but-2-enyloxy)-benzoate (2.23 g, 9.53 mmol) was dissolved in anisole (8 ml) and the mixture stirred and held at reflux for 4 days. The solvent was removed in vacuo and the residue subjected to column chromatography on silica. Elution with 20% ethyl acetate in petroleum ether afforded ethyl 3-(1,2-dimethyl-allyl)-4-hydroxy-benzoate (600 mg, 27%) as a colorless solid. 1H NMR (DMSO-d6) 10.32 (1H, br s), 7.67 (1H, dd), 7.62 (1H, s), 6.90 (1H, d), 4.90 (1H, s), 4.85 (1H, s), 4.25 (2H, q), 3.75 (1H, q), 1.61 (3H, s), 1.30 (3H, t), 1.26 (3H, d). MS: [M+H]+ 235.

Workup

  1. temperatureat reflux for 4 days
  2. customThe solvent was removed in vacuo
  3. washElution with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-294e68f49be34708990874cfeae1f384
Source dataset
uspto-grants-2014_07
Patent number
US08779132B2

Reaction notes

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